


Tales of a Deadman

by ALPHAwolf



Series: OC Drabble [3]
Category: Pirates of the Caribbean (Movies), PotC
Genre: Captain x cabin boy, Curious Jack, Loss of Virginity, M/M, Smut, Storytelling, blatant disregard for shirts, happy misunderstandings, jack has a drinking problem, post- deadman tell no tales
Language: English
Status: Completed
Published: 2018-09-30
Updated: 2018-09-30
Packaged: 2019-07-20 14:09:26
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,355
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16138871
Author URL: https://archiveofourown.org/users/ALPHAwolf/pseuds/ALPHAwolf
Summary: Jack loves telling stories, his new cabin boy loves hearing them.





	Tales of a Deadman

**Author's Note:**

> This was inspired by this post on Tumblr- http://becauseitisjohnnydepp.tumblr.com/post/137516302002/when-people-talk-about-your-portrayal-of-jack

Aesthetic available! -<https://alphaalnitak.tumblr.com/post/178591128125/aesthetic-for-my-fic-tales-of-a-deadman-jack>

 

* * *

 

 

Crisp sea air filled the Pearl’s blacken sails, her Captain standing tall at the helm, wheel in hand and monkey on his shoulder.

Finally, after everything, he had his ship back all to himself, no Barbossa to haggle with. Lizzy and Will were happily reunited on land (ew), and the ocean was liberated of all her curses, laid out before him. He was free to go anywhere, do anything, maybe even drop in to the Isle de Muerta and see if breaking the trident had lifted the voodoo on those lovely shiny pennies.

They’d just finished restocking after the whole harrowing ordeal, their usual Tortuga run. A few of the crew had jumped ship, and some new members had joined them on their yearly voyage to Singapore, a two month sail. He honestly couldn’t remember hiring half of them, but then he’d taken to drinking a little bit more than usual, what with Will and Liz all merry while he sailed the sea all on his lonesome, just him the Pearl and the seven seas. And Gibbs of course, and Barbossa’s damn monkey, which refused to leave his side. Still, the company of a crew was nothing quite like the company of a lady, something dear William was probably getting more than his fill of right about now. Hopefully he too had appealed to his more carnal desires before he’d left Tortuga, again he couldn’t quite recall. Though, in all honestly, he was a little more concerned if they’d stocked enough rum for his new and improved drinking habits.

So caught up in his musings, he hardly noted the ships new navigator coming up to relieve him till he was standing right beside him.

“Ah, very good.” Jack stepped aside and swaggered down the rocky steps towards the deck. They seemed to be in constant motion, more than he was used to at least, and he found himself stumbling at the base, the monkey on his shoulder screeching at him in detest as he bumped into a shipmate he most certainly did not recognise.

He had to do a double take, noting Mr Gibbs appeared to be showing the lad around. The young man looked back at him nervously as Jack turned to his first mate.

“Who’s this?” He found himself slurring slightly to his own ears.

“He’s the new cabin boy you hired, Cap’n, never been on a ship before.” Gibbs explained, Sparrow looking back at the ‘boy’.

“I hired you?” He nodded, his eyes flicking curiously to the monkey as Jack looked him up and down.

“Bit old for a cabin boy isn’ he?” He had to be at least Will and Liz’s son’s age, maybe even older.

“Aye, none the less you hired ‘im.” Jack trailed his eyes back from the young man’s ratty boots to his head, concluding that he must have mistaken him for a woman trying to sneak aboard back on Tortuga, what with all the bad lighting in the tavern. Even in the sun he almost reminded him of Elizabeth when they’d first met, feature wise, what with all the soft looking skin, pink lips and pale hair.

“Um, good, well,” Jack tore his eyes away only to bring his gaze straight back, “go get me a bottle of rum, from in the hold.” He ordered, the Capuchin next to his ear seeming to make a sound of annoyed disapproval, if that was even possible.

“You have one in your hand.” The boy pointed out, and he decided to allow the retort just this once.

“Yes, but it’s half empty. Now go, shooo.” The cabin boy looked at Gibbs unsure and he pointed towards the galley door, the young man slowly disappearing below deck.

They’d work on his rate of response later, Sparrow thought inattentively, taking another long swig as he continued back on his way towards his quarters.

He stumbled inside towards the desk, allowing the door to shut itself as the ship gently swayed. Little Jack jumped off his shoulder and onto his hangy thing Barbossa had gotten him, and with an audible plunk Sparrow sat before his world map, dragging his fingers wistfully over the crisp page.

The world, his for the taking.

It became disconcerting all too quickly. He’d been everywhere, done everything. There was nothing new to discover, no curiosities to divulge. Suddenly the ocean seemed as known to him as an old lover, and not in the good way.

He pulled out his compass and placed it on the table, watching it spin till it finally settled, pointing straight to the bottle in his hand. Yep, still working, he agreed with himself, taking another chug. He could swear Barbossa’s damn simian face palmed at the sight. Wonderful, he was being judged by a monkey now.

Jack’s attention was quickly diverted as the door creaked open, his new cabin boy peaking his head inside. As their gazes met he held up the bottle he’d just fetched with a smile. The Captain immediately returned it, beckoning him in and quickly finishing the old one in a few big gulps.

The young man looked on wide eyed as the last quarter of liquid disappeared, holding the new bottle out for Jack to take. He did so gladly, popping the cork and offering it up to the other for a sip. He shook his head , standing around awkwardly, unsure of what to do as Jack took a swig of the new drink.

It burned down his throat in the sweetest way, and he let out a content sigh. The first sip was always the best. Truly, there was nothing better than the taste of fresh rum.

The moment of delight was doomed not to last as he noticed the young man stepping _towards_ the little devil monkey, naively whispering a ‘hey there little guy’ to it softly. The beast jumped from its seat to the table and charged straight for the boy, Sparrow fumbling to jump out of his seat and grab the thing before it tried ripping the poor lads face off.

The cabin boy gasped in surprise as the creature pounced on his arm, crawling straight up to his shoulder before giving his cheek a big long lick. The young man grinned and let out a little giggle, carefully moving to pet the Capuchin It made an adorable little twitter and grabbed the boy’s hand, smooshing it’s face into his palm.

Jack sat flabbergasted That bloody little thing was one of the most ill tempered creatures he’d ever met, now it was acting like this new lad was Barbossa reincarnated or something.

“Tell me, lad, what’s your name?”

“Nathaniel, sir, Nathaniel Calder.” Not a name he was familiar with, so probably not another one of Hector’s offspring, though one never could be certain.

“That’s ‘Captain’, boy,” he corrected, “‘sirs’ for the Navy, savvy?” Why did everyone always forget the captain?

Jack took another swig as Nathaniel looked at the ground sheepishly.

“And what brings you to my ship?” Sparrow asked, noting in his drunken state how the boy bit his bottom lip and appeared hesitant to reply, petting the monkey on his shoulder nervously.

“Stories.” He admitted quietly after a moment.

“Stories aye?” Jack waited patiently for him to elaborate.

“Did Hell really spit you back out?” Nathaniel asked, whispering as though it was some great secret.

“Aye love.” Had he said love? Must have been the rum mixing his words. The cabin boy must have assumed so too because he only seemed shocked a moment before he was poking curiously once again.

“And you faced the Kraken?”

“Beastie swallowed me whole.” The brond looked as though he wasn’t quite sure if he believed him, but was delightedly intrigued all the same.

“How? How did it happen?” Jack grinned, stories already lining up to jump off his tongue. He gestured invitingly for the young man to take a seat, slightly surprised when he plonked himself right down on the floor in front of him, looking like an excited child, save for the monkey sitting on his head searching for fleas.

He listened with rapt attention as Jack retold his story from the black spot to the feeling of being devoured. Sometimes he’d ask questions or look on with disbelief, but not once did he say that it couldn’t be true. It was a nice change from the usual naysayers.

By the time the tale was done little Jack had fallen asleep on Nathaniel’s lap, and the boy carefully carried him over to his nest with the upmost care. He thanked him quietly for the story and left to help make dinner with a smile, images of the Kraken and tentacle faced men swimming about his mind

Jack leaned back in his chair after the young man left, finding himself strangely content as he popped the cork back on the bottle of rum he’d barely drunk.

 

§

 

He made a habit of sending his cabin boy to fetch him a drink at the end of each day, inviting him to stay for yet another tale of his misadventures. Nathaniel, affectionately named Nate by some of the crew, loved Jack’s stories just as much as the Captain loved telling them, even if some of them were a little hard to believe, like the roping of sea turtles together with back hair. Nate had just laughed delightedly at the tale, saying how much he’d like to meet the turtles.

Jack extrapolated details and filled in anything he couldn’t quite remember or felt just wouldn’t make the other gasp and smile enough with mistruths, waving his arms about and using anything he could within reach to express what had happened.

His cabin boy would sit on the floor looking up at him, eyes sparkling with delight and admiration, a monkey using him like it’s own personal climbing frame.

Nate smiled to himself, recalling the night before’s tale as he knelt on his hands and knees, scrubbing the Pearl’s deck as visions of cannibals and immortal dogs ran about his head. What kind of a story would the Captain weave tonight, he wondered? What kind of creatures would he describe?

His musings were rudely interrupted when he was abruptly yanked up on his feet by the wrist, nose violently assaulted by the overwhelming smell of rancid breath. He cringed at the sight of rotten teeth and a twisted smile, a tall weedy sailor he’d never spoken a word to hissing down at him.

“Give us a shown now won’ ya swee’art?” He demanded, grabbing the front of his shirt and suddenly ripping it open. Nate yelped and tore himself out of the man’s grip, covering the opening defensively as he stared back in terror.

He’d never learnt how to defend himself, and he was completely unarmed. Confused and feeling strangely violated he looked around desperately for something he could use against the other, stepping back towards the edge of the ship as the pirate advanced slowly.

Nothing caught his eyes but the brush and bucket, both of which were now too far out of his reach. He did however note the three other crew members watching, unsure if they were excited or considering if they should step in. Either way they did nothing to help.

Nate swallowed, backed up against the railing so hard he was hanging out over the side with the sailor almost between his legs.

Suddenly there was a shrill screech, and little Jack came barrelling towards them along the railing at full speed, jumping onto Nate’s shoulder and letting out a bloodcurdling howl.

The man flinched back and almost fell flat on his backside from the unexpected fright of a monkey’s teeth so close the devil could have bitten off his nose.

“Now what be going on ‘ere?!” Nate let out a relieved sigh as Gibbs appeared, having been alerted by the hellish noise.

The rest of the crew quickly returned to their duties as he stepped in beside the tall pirate.

“I’s just gettin' to know the Cap'ns favourite a li'l be'er.” He explained with what he must have thought was a charming grin. It made Nate cringe.

“Aye, well you’ll do better to keep ur hands to urself.” Gibbs warned. The sailor’s expression darkened, but he backed away with a scowl, returning to whatever task he had been doing before.

Mr Gibbs sent him a smile and he returned it appreciatively, realising he’d begun nervously petting the Capuchin who was protectively hugging the side of his face.

He went back to his chore, albeit a little shaken and very confuse.

Nate found himself far more vigilant the rest of day and avoided most of the crew, constantly petting the monkey on his shoulder in an effort to sooth himself.

As usual after dinner, which he decidedly spent in the galley with little Jack rather than with his shipmates, he went down into the hold and retrieved a fresh bottle of grog, taking it to the Captain’s quarters.

Jack was already waiting for him, sitting rather regally for a pirate on his bed- his favourite place to storytell from.

He noted the young man’s appearance quizzically as he took the drink from him.

“So that’s where the monkey got to... What happen’ to ur shirt?”

“It, err, got caught on a hook.” He lied as Jack took a drink, sitting himself down on the floor. If the Captain sensed his untruth he decidedly didn’t comment, instead beginning to tell him the secret of the Devil’s Triangle.

It’s one of his best, and yet Nate doesn’t seem as excited as usual. His smile was forced, he didn’t ask a single questions, and his eyes seem strangely vacant. Even little Jack couldn’t seem to get his attention, struggling to move the young man’s hand himself for a pat.

Sparrow finished the tale none the less and took another drink before he decides to press.

“So what has you vexed, lad?” He asked, Nate seeming hesitant to reply.

“It’s nothing, just... Something weird happened today.”

“Good weird?” Jack asked hopefully.

“No.” The boy admitted, his Captain giving him an expectant look. “My shirt didn’t get torn by a hook,” he confessed sheepishly, “one of the crew did it. He said he wanted me to give him a show? I still don’t understand what he was talking about.” Nate explained, looking troubled. “Mr Gibbs stopped him from doing anything else.” Little Jack screeched from his lap and the boy smiled, “And little Jack scared him off for me.”

“Must be scurvy,” The Captain explained, taking another sip and getting up off the bed, “probably lost his marbles.” He was searching avidly through a chest of fabrics now. “Still, can’ have crew members attacking other crew members, ah.” he pulled out a clean white cotton shirt, little frills on the front and sleeves. Probably one of Barboassa’s old ones, so it would be a little big, but it would do. He chucked it at the young pirate on the floor. “Here, I’ll see he knows not to do it again.”

“Thank you.” Nate replied quietly with a grateful smile, holding the shirt close. “Could I... change here?” Jack gestured openly for him to go right ahead and he quickly got up, going to hide behind a decorative cloth hanging from the frame of the Captain’s four-post bed. Jack furrowed his brows at the modest behaviour, surprised as even the monkey covered over it’s eyes.

Sparrow watched as the boy’s candle lit silhouette moved, pulling off his old shirt and sliding on the new one. He stepped back out from behind the drapery after looking himself over, carrying his old rag and wearing a shy smile, the oversized shirt hanging from his thin frame.

“Um...” He looked at the cloth in his hands, unsure what to do with it. Jack took it from him and threw it atop the chest, shocked when the monkey shot past, grabbing the item of clothing and running off to it’s little nest, adding the shirt to it’s small hoard.

“Thank you for the story, and the shirt.” Nate farewelled as he usually did after recovering from the sight.

“Anything for rum.” Jack replied, swallowing a mouthful as the young man laughed.

It was soft, musical. What he might expect a mermaids titter to sound like, if the evil creatures were indeed capable of making such a sound.

The cabin boy left quietly after sending him one last shy smile, and once he’d disappeared Jack realised the Capuchin had already fallen asleep wrapped up in the young man’s old shirt.

 

§

 

He asks Gibbs about the sailor who attacked Nate the next day and has the man keelhauled before breakfast.

He wasn’t usually one for such punishments, but it was a crew vote between being keelhauled or whipped, and evidently they all just didn’t seem to like the fellow. He’d survived, to some’s disappointment, but he appeared to have learnt his lesson, sulking fearfully and keeping a good distance from Nate.

Jack was at the wheel with Gibbs by his side when the Cabin boy arose from the galley later that day, little Jack jumping straight off the Captain’s shoulder and bolting towards him. Jack’s almost-smile at the sight quickly fell as he noted all the men nearby giving his cabin boy strange looks.

“Mr Gibbs,”

“Aye Cap’n?” Jack watched as the monkey crawled up Nate’s leg to his shoulder, the young man smiling and allowing the beast to nuzzle his nose, completely unaware of all the gazes on him.

“What be the meaning, for all the undesirable attentions, on a certain fresh member of my crew?” He asked slowly, Gibbs smiling to himself.

“They’ve been catchin’ on, Jack.” He said, his Captain looking at him confused.

“Catching on what?”

“Well, it’s hardly easy for men to behave themselves when there’s...” he lowered his voice to a whisper, “a _lady_ aboard.” Jack’s brows furrowed, even more confused then before.

“What lady?”

“Well, ‘ _mr_ ’ Calder of course.” Gibbs was looking at him befuddled now.

“Mr Calder’s a woman?” He asked wide eyed, his first mate mirroring his shock.

“Well ur the one’s been invitin’ im’ to ur room ev’ry night! All that favouritism, we all just assumed the two of you were...” he gave him a look and Jack’s mouth nearly fell open.

A moment of awkward silence ensued, his eyes turning to the rail Nate was now leaning against, drinking clean water from a bottle. The liquid made his usually dry lips glisten in the setting sun. Jack quickly looked away.

“I assure you Mr Gibbs, the only seduction going on behind that door, is seductive storytelling.”

“I see, Cap’n.” Another awkward minute of quiet followed, and he couldn’t help turning his gaze back to his cabin boy. Gibbs was staring too, no doubt the same query on his mind.

“So, not a woman?” Gibbs asked.

“Not as far as I know.” Jack replied, though the other certainly had the frame for it.

He was rather curious now, watching Nate watch the sunset wistfully. Even from where he was he could see the ocean reflected in the cabin boy’s eyes, almost as beautiful as the ocean herself.

Perhaps he was a she? It would explain the hiding in order to change shirts... Still, there was only one way to be sure.

“Take the wheel, Mr Gibbs, I’ve some curiosities to allay.”

“Aye Cap’n.” Gibbs watched with rapture as his Captain sauntered down to the deck and over to where Nate stood. The cabin boy smiled once he noticed him, Jack leaning back casually against the rail.

“Do you have a job for me, Captain?”

“Hm? No no, just, enjoying the view.” The young man/woman? Chuckled at this.

“You’re facing the wrong way.” He/she? pointed out fondly.

“No I’m not... I simply, am, the view.” He managed to rebut, making Nate laugh again. He was certain the sunset was lovely, as the other seemed to have all his/her/their? attention on it, which gave him the time to try and subtly angle himself in a way so he might be able to see down the other’s shirt. It quickly proved far to arduous a task with the ruffles on the other’s collar and the Capuchin practically hugging on his/her neck.

Well, he was left with no other option. He’d just have to get the clothes off, and the monkey.

“Have you sailed to the edge?” Nate unexpectedly asked, distracting his thoughts.

“Not I, but some of the crew did, lead by Barbossa. ‘S how they fetched me from the locker.”

“Really?” He/she looked at him amazed.

“Aye, ‘l have Gibbs tell you the story some time.” A first hand account was always better, but that was for later. Right now he was on a quest.

“...You know, I’ve met many strange, beautiful creatures in my time-”

“Like the Kraken?”

“What, no, hideous thing, all teeth, tentacles and bad breath, no no,” he waved his hand about as if shooing a fly before leaning back in enticingly once again, “like mermaids, like Calypso ‘erself.”

Nate’s eyes sparkled like still ocean water in the morning light.

“Mermaids are real?”

“Of course!” Annoying and noisy bloodthirsty buggers, but that was a point for another story, “They’ve voices like angels, luring poor sailors to a watery grave with promise of nought... but a kiss.” He leaned in a little closer, whispering to the cabin boy who had eagerly inclined him/herself closer to hear, “I recon you’d do an a’right job as one of ‘em.”

Confusion riddled his/her expression a second before he/she realised what the other meant, Nate’s eyes going wide and cheeks turning the same hue as the sky.

There was a defending primate screech, successfully snapping Nate out of the spell of Sparrow’s gaze as he/she quickly looked away. Little Jack crawled over to the cabin boy’s left shoulder as if in an attempt to step between them.

Jack frowned. There had to be some way to temporarily get rid of that damn monkey.

“Shall we... retire early, for a tale?” The Captain asked, Nate’s heart thumping wildly in his chest.

“I-I shouldn’t, it’s probably time I go help down in the kitchen.”

“They’ll do without you,” Sparrow insisted, lowering his voice to a gravelly vox, “you can dine with me tonight.”

Nate swallowed, a shiver running down his spine. It must have been the breeze, and not the fact that he had absolutely no idea what to do with such attention. His heart felt like it was about to beat clear out his chest, and his palms had gone all sweaty. This only became worse when Sparrow took his hand, coaxing him towards his quarters.

“Mr Gibbs!” Jack suddenly called, his first mate quickly pretending he hadn’t been staring.

“Aye Captain?”

“See to it that someone fills in for Mr Calder’s afternoon duties.”

“Aye Captain.”

Nate found himself all but dragged towards the Captain’s cabin, his face feeling rather warm. More sunburn probably.

Jack pulled out a chair and gestured for him to sit at the table, surprising the young man who had up till now always been on the floor, and then took his own beside him.

There was little time for Nathaniel to be confused by the legendary pirate’s strange behaviour before he had begun reciting a new story. Nate quickly became so wrapped up in the tale of mermaids, zombies, and Black Beard himself that he completely forgot about Jack’s strange advances, writing it off as the fleeting fancy of a drunk. He was so enraptured he didn’t even notice the time passing till dinner was brought, and even then Jack continued to talk through his mouthfuls.

Like a spell time passed in the blink of an eye.

Little Jack had fallen fast asleep using Nate’s hand as a pillow by the time the Captain was near the end of his tale, Jack so soaked up in to his own storytelling he too had almost completely forgotten his intent for inviting the other in early. Thankfully the monkey was now out of the way.

“You abandoned her?” Nate asked shocked, both of them leaning in close.

“I marooned her, love. Lovely Island for it, known trade route. Couldn’t have the daughter of Blackbeard trying to make an honest man of me.” He replied simply.

“It might not have been so bad.” Nate suggested. “You could have sailed the Pearl together, travelled the world... never felt lonely late at night.” He whispered the last bit tentatively, biting at his dry bottom lip.

“Now why would I want a woman like that to keep me company,” Jack began, his voice low and secretive, “when there are creatures such as you out in the world?”

Nate went red as a lady’s dress, his mouth falling open as he failed to find any reply. And now the Captain was leaning closer, his hand dancing through the air to grace the cusp of Nate’s jaw. The cabin boy was frozen in place. What should he do!? Should he move away? Move closer? Say something? What should he say? What could he say? What did he want to say-!?

Like a shock through his system the questions all suddenly silenced, eyes wide as Captain Jack Sparrow’s mouth pressed to his.

Both their lips were dry and textured from the sea air, moving languidly like ocean water crashing against the rocks on a reef. Such courting however was short lived, Nate’s eyelids falling closed as the other’s mouth sucked him in.

Jack tasted like rum, fresh out of the bottle, his kisses as rough and wet as the water, pulling him in like a rip.

With great care Nate slipped the hand little Jack had been using as a pillow out from under the monkey’s head, moving closer and gripping the front of his Captain’s shirt like a lifeline, as though the man where anchoring him to reality.

The second they parted for a breath of air he found himself being pulled to his feet and back into another kiss, Jack’s lips hungrily devouring his. He began to lead him one step at a time by the soft hold he had on the boy, cupping his face with both hands as Nate held on tightly to the front of his clothes. Before he knew it he was being pushed onto the Captain’s bed, gasping as he landed back onto the satin sheets.

Jack crawled on top of him, taking note of the cabin boy’s heaving chest as he panted like he’d been half drowned, eyes fluttering as Sparrow quickly dived in to steal more of his air. He returned the kiss just as hungrily, moaning as the other sucked his cracked lips till they were soft and swollen, shining like the lustre of a pearl.

Jack’s hands were everywhere, sliding from his face to his waist, creeping under his shirt and up his stomach. They hesitated a moment as he came to his chest, finding it completely smooth.

No boobs? But no chest hair either... Well, he supposed it certainly wouldn’t have been the first flat chest he’d come across on a woman. Without corsets lacing then up till their bosoms exploded a lot of the the girls he’d know were rather... lacking in depth, maybe not to this extent, but still.

Continuing on his expedition he tweaked one of the other’s nipples on his way back down, rewarded with a shocked mewl.

The pants were next, sucking with the force of a Kraken down the side of the young man’s neck to make him emit the most wonderful sounds as he unlaced his britches.

Jack grinned as he sat up between the other’s legs and yanked them down, Nate letting out a surprised squeak while the other froze up the moment they slipped down and revealed the embarrassed crew member’s sex.

“Oh.”

“Wh-what?” Nate asked worriedly, pulling his shirt down to cover his nudity.

Despite everything Jack had still only been half expecting the cock he was now looking at...

Well, too late now.

“Nothing.” He didn’t waste another moment, tearing the boy’s shirt clean open as he gasped. There went another one. Hopefully he had another spare.

Jack’s lips licked and sucked down the salty skin of his torso, delighted to find the young man just as responsive as any woman, panting wantonly and angling himself up against him for more.

Sparrow quickly shook off his coat, throwing aside his weapons, holsters, and sheath The two belts were next, which he struggled with momentarily before Nate’s hands, tremoring with anticipation, came to his assistance.

His sash, rabbit pelt, and overcoat where all removed as quickly as he could manage, stopping every now and then to drop down for a deep, filthy kiss. At some point Nate removed his hat, as it kept bumping into his face, and hung it on the bed post.

Thankfully the boy only wore a shirt, pants, and shoes or they’d be there all night.

Finally Jack’s shirt was off and they were kissing again, their bare chests pressed together as Nate gasped between their lips. It was... not all together unpleasant, without breasts in between, though he did enjoy having something he could squeeze... An idea crossed his mind and his hands smoothed down to the young man’s hips, slipping underneath the other to his rear and groping the round globes of his behind.

Nate gasped and pushed up against him, his legs spreading eagerly on their own accord.

Oh, how wrong he’d been thinking the world had given him her every experience when here he was, a nice new thing he’d never done before right in front of him, practically begging to be discovered.

Nate was breathing raggedly and smiling up at him as their bodies melded together, eyes fluttering and head lolling back with a long moan as their lower bodies met.

The cabin boy was suddenly left practically naked and very confused on the other’s bed when Jack got up and made his way hurriedly over to the table. Careful not to wake the furry sleeping devil he grabbed the small saucer of olive oil, used to soften bread, and rushed back over to the mattress. He left it on the bedside by his night rum, Nate still looking at him questioningly, and kicked off his shoes, gesturing for the other to do the same.

As soon as the boy’s boots were off Jack yanked his britches the rest of the way down his legs, leaving his body bare to be plundered. He forced his thighs apart and sat comfortably on his knees between them.

“Ever done this before with a man?” Nate shook his head vigorously, unable to find his voice to admit he actually hadn’t done this before at all. “Me neither.” Jack added quietly, before diving in for another kiss. Surely it couldn’t be that different than taking a woman from behind? Right?

Nate watched face flushed as Jack slowly undid his pants, slipping them down with his underwear as the boy bit his lip at the sight of his Captain’s favourite pistol.

His legs seemed to widen instinctively, showing off his hole without thought. The Captain’s hardened length twitched, the man hurriedly pouring some of the olive oil from the saucer onto his palm and groaning as he smothered his cock in it. Sparrow sighed blissfully as he gave himself a few lazy pumps, watching Nate bite his lip till it almost bled at the sight.

The emergence of a tiny pearl of viscous white from the younger’s patient tip distracted him from his own pleasure, dipping his fingers back in the oil and gripping the boy’s thigh with his other hand, holding his cheeks apart.

Nate’s expression turned from confusion to discomfort as he slid two fingers forcefully inside, surprised by the extreme tightness around him. Right, first time, so not as loose as the horologists’ Jack was used to.

The cabin boy gasped and squirmed, expression tight as he gripped at the sheets. Jack was sliding his fingers in and out as fast as he could, which proved rather difficult due to the vice clamping around him.

Slowly but surely the other loosened up ever so slightly, and he took the chance to shove a third finger in before he tightened up again. Nate immediately whimpered and tensed, breathing raggedly and gritting his teeth.

The Captain whispered sweet nothings to calm him, half of which made absolute zero sense but then he wasn’t really in a state to pay attention with the burning in his rear. Jack’s fingers movements did become a little more gentle, and he kissed him softly as if to make up for the pain, before learning he could make him really loosen up by mouthing a specific spot on his neck.

In no time Nate was trapped between discomfort and bliss, Jack’s digits thrusting and stretching his dungbie. Sparrow noted the decrement of pained sounds and sat back to see how the other was faring.

The cabin boy was laying with his head back, mouth wide and eyes shut as he panted. His legs had gone limp, hanging open as he threaded his fingers within the blanket.

“A-ahhh-” Jack slipped the digits out and grabbed more oil, pouring it all out over the other’s thighs and crotch before smothering it all over and inside the pink ring of muscles. He watched it twitch as he pulled his hand away from the mess, rubbing his lubed hand over his cock again.

Nate swallowed as he shifted in closer, the Captain lining himself up with his opening.

“N-nnn!” It took a bit of force but he managed to push inside, grunting as the other went rigid and clutched the sheets. Nate hissed and jolted as he pressed in further, Jack’s eyes falling shut as he felt the passage around his sex _squeeze_. He was so used to being sucked in, who would have thought trying to be forced out would feel so good?

Nate whimpered and mewled as Jack gripped the bedhead, his mouth falling open as he made his way all the way to the hilt. God, the boy really was a vice, but so warm and soft it was like being sucked down someones throat, only less wet.

He felt blindly around the bedside table as Nate continued to make increasingly loud agonised sounds, knocking a few items to the floor before he managed to locate the rum. He ripped the cork off with his teeth and took a large swig, locking his mouth over the other’s and forcing him to swallow. It would alleviate the pain a little and hopefully help him quieten down. He really didn’t want that monkey waking up right now and ripping his hair out.

Nate gasped after he’d downed the rum, licking his lips before opening his eyes, staring up at his Captain. His eyes were blue as a Swiss topaz and glazed with tears, lips pink as alexandrite in candlelight. Feeling strangely fond Jack kissed him gently and held his face, the boy’s hands sliding up to rest on his shoulders as their tongues slid against one another.

He waited patiently till the other stopped making broken sounds before he slowly slid himself back out just a little, pleasure gripping him as Nate whimpered and clutched his deltoids, nails digging into his skin. Merciless, he pushed straight back in, the young man gasping as his thighs tensed up, their lower bodies meeting roughly. Jack couldn’t help a guttural moan, repeating the motion and slipping out even further this time.

Before he could help himself he was thrusting in and out, one hand gripping the boy’s thigh and the other holding his hip, keeping him open and in place.

“B-bloody pirate-!” Nate gasped, clenching his teeth as the other smirked, taking a hold of his wilted sex and beginning to pump. The young man quickly changed his tune, mewling and squirming beneath him like a netted mermaid out of water.

Slowly the pain seemed to fade and he began gasping for a different reason, laying defenceless and needy beneath him with his legs spread wide and his back arched. Jack noticed the change as soon as the other began moving with him, panting and holding him close as he impaled him from behind.

Jack thrust inside him in perfect sync with the crashing waves against the ship, and for a moment they were one with the ocean as they held one another and cried out in ecstasy.

 

§

 

Jack stood, the salt wind in his hair and a small smile on his lips, guiding the Pearl to his will by her wheel under the morning sun.

Mr Gibbs came to stand beside him, both’s eyes turning to the deck as the Captain’s cabin door opened tentatively. Nate stepped out, looking a thorough mess with another new shirt and little Jack on his shoulder. The cloth hung open showing his sucker mark ridden collar and neck, which the monkey seemed to be trying to help cover over.

He went pink as a few of the crews eyes turned towards him, hurrying to find a task to busy himself with, despite his rather obvious limp.

“So...” Gibbs began, giving his Captain a knowing look.

“Not a woman.” Jack confirmed without restraint, his first mates eyes going wide as the barrel of a canon.

“Not a woman?” He gasped in disbelief.

“Most definitely not a woman.”

“But, urr...” there was a moment of silence as Jack smiled to himself.

“What can I say, Mr Gibbs, these long voyages are testing on the boundaries of a man’s desire.”

“It’s only been two weeks sir.” Jack grinned widely, catching his cabin boy’s eye. The young man bit his lip and quickly looked away with coy upturned lips.

“Aye.” And what a lovely month and a half of moonlight storytelling he had to look forward to.

 

 

**Author's Note:**

> Hope you liked! Plez Kudos!  
> also Nate is one of my oc's, if you'd like to use him please ask me first ;)


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